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Showing NP-Card for pinol (NP0306648)

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Record Information
Version2.0
Created at2022-09-10 23:15:34 UTC
Updated at2022-09-10 23:15:34 UTC
NP-MRD IDNP0306648
Secondary Accession NumbersNone
Natural Product Identification
Common Namepinol
DescriptionXi-Pinol belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen. Xi-Pinol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, xi-Pinol has been detected, but not quantified in, citrus. pinol is found in Agathosma betulina. This could make XI-pinol a potential biomarker for the consumption of these foods.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0306648 (pinol)


  Mrv0541 02241211572D          

 11 12  0  0  0  0            999 V2000
   -0.3554    0.5645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3554   -0.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3583   -0.6733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0706   -0.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0706    0.5645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3583    0.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3583    1.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0706    0.1519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3569   -1.0858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7694   -1.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0556   -1.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1  8  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  9  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
Download

3D MOL for NP0306648 (pinol)

     RDKit          3D

 27 28  0  0  0  0  0  0  0  0999 V2000
    3.0785    1.1469    0.0122 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8552    0.3389   -0.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6678   -0.6852   -0.8911 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3029   -1.2094   -1.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6407   -1.0920   -0.0419 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2018   -0.8428    1.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6721    0.5770    0.8763 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3013    1.1431    0.0952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3478    0.2716   -0.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1930    0.4704   -1.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1536    0.3133    1.2517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2226    1.5232    1.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9873    0.5229   -0.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0164    2.0370   -0.6387 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5605   -1.1172   -1.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3937   -2.2808   -1.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0525   -0.6494   -2.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3365   -1.9162    0.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4056   -0.8685    2.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0333   -1.5479    1.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9471    1.1462    1.7614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1465    0.9745   -0.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7468    1.1079   -2.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5502   -0.5030   -1.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0051    1.0133    1.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5755    0.8083    2.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4839   -0.6823    1.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  7  2  1  0
  9  5  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  1
  6 19  1  0
  6 20  1  0
  7 21  1  1
 10 22  1  0
 10 23  1  0
 10 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
M  END
Download

3D SDF for NP0306648 (pinol)


  Mrv0541 02241211572D          

 11 12  0  0  0  0            999 V2000
   -0.3554    0.5645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3554   -0.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3583   -0.6733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0706   -0.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0706    0.5645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3583    0.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3583    1.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0706    0.1519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3569   -1.0858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7694   -1.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0556   -1.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1  8  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  9  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0306648

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CCC2CC1OC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O/c1-7-4-5-8-6-9(7)11-10(8,2)3/h4,8-9H,5-6H2,1-3H3

> <INCHI_KEY>
SKBXVAOMEVOTGJ-UHFFFAOYSA-N

> <FORMULA>
C10H16O

> <MOLECULAR_WEIGHT>
152.2334

> <EXACT_MASS>
152.120115134

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
17.950018992051724

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,7,7-trimethyl-6-oxabicyclo[3.2.1]oct-3-ene

> <ALOGPS_LOGP>
3.09

> <JCHEM_LOGP>
2.1051900130000005

> <ALOGPS_LOGS>
-2.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.215516341723459

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
46.467299999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.77e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pinol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0306648 (pinol)

Download
PDB for NP0306648 (pinol)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.663   1.054   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.663  -0.486   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.669  -1.257   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.998  -0.486   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.998   1.054   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.669   1.821   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.669   3.362   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.998   0.284   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.666  -2.027   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.436  -3.362   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.104  -3.362   0.000  0.00  0.00           C+0
CONECT    1    2    6    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6                                                            
CONECT    8    1    9                                                       
CONECT    9    3    8   10   11                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

Download
3D PDB for NP0306648 (pinol)
Download
SMILES for NP0306648 (pinol)
CC1=CCC2CC1OC2(C)C
Download
INCHI for NP0306648 (pinol)
InChI=1S/C10H16O/c1-7-4-5-8-6-9(7)11-10(8,2)3/h4,8-9H,5-6H2,1-3H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC10H16O
Average Mass152.2334 Da
Monoisotopic Mass152.12012 Da
IUPAC Name4,7,7-trimethyl-6-oxabicyclo[3.2.1]oct-3-ene
Traditional Namepinol
CAS Registry NumberNot Available
SMILES
CC1=CCC2CC1OC2(C)C
InChI Identifier
InChI=1S/C10H16O/c1-7-4-5-8-6-9(7)11-10(8,2)3/h4,8-9H,5-6H2,1-3H3
InChI KeySKBXVAOMEVOTGJ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Agathosma betulinaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassTetrahydrofurans  
Sub ClassNot Available
Direct ParentTetrahydrofurans  
Alternative Parents
Substituents
  • Tetrahydrofuran
    • 

  • Oxacycle
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.09ALOGPS
logP2.11ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity46.47 m³·mol⁻¹ChemAxon
Polarizability17.95 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0038251  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB017544  
KNApSAcK IDNot Available
Chemspider ID91391  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101153  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]